Five Times Blair Bailed Chuck Out of Jail
by Diamondinsanity
Summary: Five times Blair bailed Chuck out of jail, and one time they both had to be bailed out.
1. Indecent Exposure

**Title: Five Times Blair Bailed Chuck Out of Jail (and One Time She Didn't) [1/6]**

**Author: Diamondinsanity/karmawiccan**

**Rating: PG-13/T**

**Disclaimer: I own nothing.**

**Pairing: Chuck/Blair, Blair/Nate**

**Spoilers: None really.**

**Timeline: Pre-series—Sophomore year**

**Word Count: 2465**

**Summary: Five times Blair had to pick Chuck up from jail, and one time they both needed to be picked up from jail.**

**Author's Notes: This is what happens when I should be studying for my juvenile delinquency exam…**

"I need you to get me from the 101st precinct." Chuck's voice greeted her without so much as a hello. "Oh. And could you bring me clothes?"

Blair blinked as the line when dead and immediately decided that she wasn't picking him up from a precinct. She didn't even know where the 101st precinct was. So despite the fact that she had decided not to pick him up, she googled it only to find that it was in Queens.

She was most definitely not going to Queens to pick up Chuck Bass. Like she would let anyone catch her going to Queens, and tipping off Gossip Girl. And yet she couldn't help but wonder what the hell he was doing in Queens that got him arrested.

Sighing she checked the time. It was two in the morning. Nope. There was no way that she was picking him up from a police station in Queens at two in the morning. And yet she stripped out of her nightdress and into a pair of jeans and a sweater.

"Nate's in the Hamptons." She reasoned out loud as she grabbed her purse. "He would want me to pick his best friend up from jail." Still even as she said that, she couldn't help but to wonder why he hadn't just called one of his many whores. Or Georgina. Georgina always loved seeing him down on his luck. He should have called Georgina.

Silently she snuck through the penthouse, fearing that the sound of the elevator would awake one of her parents and she would be caught trying to rescue Chuck Bass from Queens. When she didn't hear either parent come out of their room, she slid into the elevator, saying a quick prayer in hopes she would get out of this without anyone knowing she was going to Queens.

She made sure she didn't see anyone she knew before hailing a cab and heading to the Palace. Suddenly she found herself wondering again why she was doing this. He was only her boyfriend's best friend, and Chuck Bass; no one that important. And yet she couldn't help but to know that he would do the same thing for her. Not that she would ever get arrested in Queens of course. She, unlike Chuck, has taste. But bailing each other out of jams did seem to be their thing lately. She just couldn't figure out how it went from social destruction to jail.

Once the cab was at the Palace, she double checked for anyone who looked like they read Gossip Girl before dashing out of the cab. She stalked over to the concierge desk and bit her lip softly. A year or so ago she and Chuck had come up with an emergency phrase so she could get his spare key in order to sneak Drunk Nate home when Chuck was out on his 'house calls.' It had been a joke suggestion at the time. She hadn't actually believed that Chuck would want her to use _that_ phrase to get his spare key. And yet he'd been only too eager to use it. Apparently he liked making her uncomfortable.

A part of her didn't think getting Chuck's clothes was worth getting the spare key that he wouldn't let her keep (he said that he didn't want her walking in on him with anyone, and that the key was to be kept at the front desk and only used to pick Nate up). But she did it any way. After all, this meant that she got to dress him. It had possibilities.

"Hi. I forgot my key to my boyfriend's suite. Room 1812." She said in her most convincing voice, knowing very well that claiming to be Chuck's girlfriend was not convincing to anyone who actually knew him. But that was the joke she got stuck with. If only she hadn't made the mistake of saying that dating Nate was like dating Chuck as well because they were almost always together and she always had to put up with both of their drunk asses.

The concierge looked at her, cocking an eyebrow. He knew very well whose suite that was. Who didn't know whose suite that was?

She was going to kill Chuck once he was out of jail. "I'm Blair." She shot him a 'don't you recognize me?' look. "Blair Waldorf." She added for clarification as she flashed him her id before pursing her lips together in fake suspicion. "I am the only woman on that list, aren't?"

The man blanched for a moment before nodding. "Of course you are, Miss Waldorf. I'm sorry." He handed her the spare key. "Did you want me to ring up there to make sure he's there?"

Blair looked at him. Obviously Chuck had trained the front desk well. When you had as many women as Chuck did, she figured it was something you needed to do. But she hadn't been making things up when she said she was the only woman on his 'list.' The only people on it were her, Nate and his father. Still, she couldn't help but to be impressed by the concierge's dedication to not cock blocking Chuck. "He's not up there obviously. Otherwise he would have given me his key." She smiled sweetly at him. "He asked me to pick up his scarf for him since we need it tonight."

Not waiting for the man's reaction, she stalked right up to the elevator, grateful to be hidden from the world. Like she wanted to be seen going to Chuck's suite at two in the morning. That just had scandal written all over it, and that was the last thing that she needed right now.

Once she was in his suite, she immediately went to his closet, making a face at the bright colors that assaulted her. Blair grinned as she survived her options. Oh the possibilities. At first she thought about making him wear something heinous, but quickly dismissed that option. After all, she was going to be seen with him, and she couldn't be seen with a bad dresser (even though some days he was pushing his luck with the clothes he chose).

Quickly she grabbed a pair of jeans, knowing that he would hate it. Chuck Bass did not wear jeans. Why he had a pair she did not know, but she was going to make him wear them. She also grabbed a sweater she knew he hated because Nate's mother had given it to him before dashing out of his suite and breaking the cardinal rule. She would not be returning his key this time.

She was in another cab and half way to Queens when she got the text message.

**Spotted: B asking the concierge at the Palace for her boy friend's key. 1812, B? Last time we checked that was C's suite, and N was still in the Hamptons. Sleeping with the best friend, B? Classy.**

"Does that bitch ever sleep?" Blair wondered out loud as she stared out the cab's window. That was it. She was going to kill Chuck.

When the cab arrived at the precinct, Blair all but stormed inside the building. She glanced around quickly to figure out her surroundings before marching up to the counter and throwing down Chuck's clothes. "I'm here to pick up my boyfriend." She all but ground out the words, surprising herself that she'd used the word 'boyfriend.' But then again it was an emergency…

The officer behind the counter eyed the clothes. "Let me guess. Charles Bass." He said dryly. "You here to get the girl, too? She's driving me insane. Can I see your ID?"

She frowned at him as she handed him the ID that said she was eighteen. "What girl? He wasn't with a Serena was he?" That was the last situation she wanted: both of her closest friends in jail. Not that it would be Serena since she was in Connecticut. But if it wasn't Serena, she was going to kill him. How dare he ask her to come to Queens of all places and pick up him and another woman? That was ridiculous. Especially if she was supposed to be playing his girlfriend.

"No." The officer frowned slightly as he handed her back her ID. "A Georgina."

Blair's face hardened. "She can stay behind bars." She lowered her voice slightly. "Where she belongs."

The officer laughed, figuring it just to be a lovers' spat. "I'll go get him."

She rolled her eyes as she leaned against the counter, waiting for him to come out. Of course he was with Georgina. It all made sense now. That didn't mean she liked it though.

"Bass!" She heard the officer's voice in the distance. "Your girlfriend's here. Time to go."

Blair leaned further over the counter as she attempted to hear what Chuck's reaction would be.

"Finally."

She sighed in relief that she hadn't overstepped any weird rule of theirs.

"No. Just Bass." The officer said firmly, and Georgina started swearing in the background.

"Sorry, G." Chuck's voice echoed out to her. "I guess B just doesn't like you. I wonder why."

Georgina's swearing began again.

Blair leaned further over the counter to attempt to hear more. In the process she leaned too far and the next thing she knew she was on the ground on the other side of the counter. "Ow…" She mumbled.

"Couldn't wait to see me, dear?"

She glanced up to see Chuck standing over her. Wait. Scratch that. Chuck standing over her wearing grey sweatpants. She blinked.

He rolled his eyes at her before grabbing her hands and pulling her to her feet.

Blair kept staring at him now noticing that he was wearing a grey t-shirt that said 'Police Department' on it. She blinked again. "Chuck…" She began slowly. "Where are your clothes?"

He ignored her and continued walking around the corner.

That was when she remembered that she was mad at him.

She stormed around the counter, and before he could reach his clothes began hitting him with her purse. "Georgina Sparks, Chuck? What the hell where you thinking?" She paused for a moment before continuing smacking him with her purse. "And how the hell did you end up in Queens."

Much to her surprise, he didn't try to fight her off. He just let her hit him with her purse as he studied her. "I was trying to get my clothes back." He stated.

Blair stared. "Why weren't your clothes on?" She suddenly froze. "Georgina?" She groaned. "Again? That girl is a walking STD. But then again so are you. I suppose its fitting." She hissed under her breath.

Chuck rolled his eyes. "We were playing strip poker. At least we were until she decided strip running was more enticing." He spotted the clothes on the counter. "Are these mine?" When he realized what she'd given him, he looked at her. "I'm not wearing that."

A sweet smile slipped onto her features. "Well, you're not going out in public in sweatpants. I won't allow it."

He grumbled for a moment before disappearing into the bathroom.

The officer looked at her. "So how long have you and Casanova been together?"

She pursed her lips together as she pretended to think about it. "Since kindergarten." That was how long ago Nate had stuck him with her. Dating Nate really had forced her to at least have to pretend to be Chuck's girlfriend when the situation called for it, and it was disgusting. But she did it was a smile on her face. Well… A fake one at least.

"So you allow your boyfriend to go streaking with your friends?" He asked her with a frown.

Blair faked a laugh. "Oh. Georgina and I aren't friends. And he's my ex-boyfriend after this."

"It was only strip poker."

Surprised to hear Chuck's voice, Blair spun around, and immediately began laughing at Chuck. There he stood barefoot wearing jeans and a brown turtle neck sweater. He looked ridiculous, and Blair suddenly felt like being woken up at two in the morning had been worth it.

"Can we go now?" Chuck all but whined when the officer started laughing as well.

Blair only smirked before sashaying out of the precinct, feeling Chuck following her like a puppy. She didn't say a word to him as she hailed a cab.

"You didn't bring me shoes, did you?"

She turned and raised an eyebrow at him. "I always knew that you would lose your pants without supervision." She replied before walking towards the cab. "And no."

He grumbled under his breath the entire way to the hotel.

"I could have left you there with Georgina."

He stopped grumbling just in time to get out of the cab, and then held his hand out expectantly to her. "Well, come on."

Blair stared at him. "I am not sleeping with you."

Chuck rolled his eyes. "No, but I'm also not going inside without an excuse for not having shoes on. So help me pretend to limp."

A laugh immediately escaped Blair's lips and she slid out of the cab. "Fine." She said with a shake of her head as she wrapped an arm around Chuck's waist and let him lean against her. "The things I do for you, Bass."

He snorted. "I make your life interesting, Waldorf."

Xoxo

The next morning Blair woke up, sprawled across Chuck's bed, a vague memory of being too tired to go home dancing through her head. She stretched, and glanced over to find Chuck sleeping on the couch. And people said he wasn't gentlemanly. You just had to threaten him with castration first.

Sighing when she saw that it was nearly noon, she fell back against his pillows before deciding to risk it and check Gossip Girl to see how bad the damage was.

**Spotted: B and C returning to the Palace- **

She exited from the message deciding suddenly that she didn't want to know any more. Didn't people have better things to do at four in the morning?

Sighing she checked for the inevitable message from Nate, expecting him to yell at her. She didn't have one. In fact, she didn't get a message from him all day. Nate didn't care that Gossip Girl thought she was dating his best friend.

She didn't know whether to be annoyed or pleased that he didn't believe Gossip Girl. Her boyfriend was hard to read ever since Serena went to boarding school.

That's when it dawned on her: some days it was easier to pretend to be Chuck's girlfriend than to actually be Nate's. Vaguely she wondered what that meant about her and Nate. And then she decided that if Chuck ever called her from jail again, she wouldn't pick him up. It just made things too complicated.


	2. Minor Under the Influence

**Title: Five Times Blair Bailed Chuck Out of Jail (and One Time She Didn't) [2/6]**

**Author: Diamondinsanity/karmawiccan**

**Rating: PG-13/T**

**Pairing: Chuck/Blair, Blair/Nate**

**Word count: 3191**

**Spoilers: None**

**Timeline: Pre-series/sophomore year**

**Summary: Five times Blair bailed Chuck out of jail and one time they both needed to be bailed out of jail. **

**Notes: Follows part 1. And yes, I realize that two weeks is a short time to be arrested twice, but really? He's Chuck Bass. I'm surprised that he doesn't get arrested on the show as much as he probably should…**

* * *

Two weeks passed by without any middle of the night phone calls from Chuck Bass. School was in full swing, and Nate was kind of back to normal. He still hadn't mentioned anything about the Gossip Girl blast, which bothered Blair slightly. Shouldn't he care that she'd been at Chuck's suite at two in the morning or that she'd spent the night? He'd been acting so odd ever since Serena ran off to boarding school without saying a word.

Although she was glad that she hadn't had to put up with any of Chuck's bullshit these past two weeks, she did miss him. It was boring without him hanging around her, but they hadn't been speaking since she left the Palace that morning. He was upset that Gossip Girl caught him wearing jeans, and Blair was still upset that he had been with Georgina. She just couldn't figure out why her best friends kept spending their time with that whore. So until he had a good reason to explain why he'd been hanging out with Georgina, she was not speaking to him. And he informed her that he was not speaking to her until she sent a retraction to Gossip Girl stating that he was only wearing jeans because she'd made him wear them, which frankly in Blair's opinion would just make the rumors about their 'relationship' worse.

So she was completely surprised when Nelly's "Hot in Here" began playing -- A ring tone Chuck had placed on her phone for him without warning her he'd done it until he'd purposely called her on the steps one day at lunch just to watch her reaction; she hadn't bothered to change it since then. She stared at her phone in complete confusion as she tried to figure out why Chuck would be calling now. It was ten thirty at night on a Thursday. Normal people were getting ready for bed. Not calling their estranged best friend. So she just listened to his ring tone.

"It's getting hot in here. So hot. So take off all your clothes. I am getting so hot. I wanna take my clothes off."

Even though she had decided not to answer the phone, she just kept staring at it. A sigh instinctively escaped her lips when it stopped ringing. Impatiently she waited to hear the familiar ding that informed her of a new voice mail, but it never came. Instead her phone started ringing again. She swore under her breath before snapping it open.

"What!" She all but yelled.

Instead of hearing him scream back at her, he just started laughing on the other line. "Bllllllllair. Blair, Blair, Blair."

She stared incredulously at her phone. "Chuck Bass, are you drunk on a Thursday night?" She hissed into the phone, unable to believe him. Who got drunk on a school night?

He laughed again—a harsh uncharacteristic laugh that sounded completely foreign to her. That was not what Chuck Bass was supposed to sound like. "Drunk is such a harsh word, B. I prefer…" He paused as he tried to figure out what word it was that he preferred. "I prefer buzzed."

Suddenly Blair had the familiar 'I'm going to kill Chuck Bass' feeling wash over her. "How much have you had to drink and where is the whore that is supposed to be taking care of you?" She asked, the question sounding a little harsher than she meant for it to.

"I sent her home. She was booooooooring." He laughed again, and then there was a loud crash.

Blair's grip on her phone tightened. "Chuck! What was that?" She asked, unable to hide her sudden worry. He was always worse than Serena when he was truly drunk, which was a rare occasion. Normally he knew when to stop. She didn't know why he'd just let himself go like this.

Another laugh. "It's alright. The ground just tripped me but the trash cans broke my fall." There was another crash. "But now they're in the street."

Blair was already stripping out of her nightdress and into the dress she'd worn earlier that day. "Chuck, where are you? I'm coming to get you."

There was silence for a moment as he tried to figure out where the hell he was. "I'm…" He laughed again. "I'm not sure where I am, but I'm not in Queens this time I can tell you that." There was another laugh followed by a loud crash.

"Chuck! Stop throwing things!" Blair all but screamed into the phone. "What are you near? What stores?"

Another crash. One that sounded a lot like glass breaking. "I'm still by the bar I was at." He said before swearing loudly as the sound of breaking glass slipped across the line again.

Blair grabbed her purse and was throwing her heels on. "Okay, what bar?"

But she never did find out. That was when she heard the sirens, and Chuck's "Oh shit…"

She blanched. "Chuck! What's going on?"

There was a sound of a door slamming.

"I think I'm being arrested."

The line went dead.

"What do you mean you're being arrested!!!!" She screamed into the phone even though she knew he couldn't hear her. God, this was just what she needed to happen tonight. Frustrated, she screamed, and threw her cell phone into the wall.

The door to her room slowly opened. "Blair-bear? What's wrong?"

Blair immediately spun around and threw herself into her father's arms. "I think Chuck just got arrested." She couldn't help the words that immediately spilled out of her mouth. When it came to her father, she just instinctively wanted him to make everything better. She wasn't sure how he'd react to the fact that Chuck had been arrested, but then again it was Chuck Bass…

Harold pulled away for a moment and studied his daughter curiously for a moment. "What do you mean you think he got arrested?" He asked in complete confusion, closing the door so Eleanor couldn't hear what they were talking about. They both knew very well that Eleanor didn't approve of Blair having any form of communication with the younger Bass, and knowing he'd been arrested would not help Blair's argument that he wasn't that bad.

"I was on the phone with him when they police showed up..." She said slowly, not sure where her father was going with this. "His dad is in California…" She threw out, not sure if that would be important to whatever it was that was going through her father's mind.

Her father merely pulled out his cell phone, waving a hand as if to dismiss his daughter's comment about Bart. "Do you know where he was?"

She thought for a moment. "Knowing him? Probably midtown." She couldn't hide the disgust from her voice.

Harold nodded. "Stay here." Was all her said before disappearing from her room.

* * *

Xoxo

* * *

Although Blair trusted her father to fix everything, the next hour and a half was the most painful hour and a half of her life. She hated not being in control almost more than she hated the fact that she hadn't physically been there when he was arrested. Being on the phone with him and knowing what was going to happen was one of the worst things she'd ever experienced. There was nothing like being completely useless to make you feel completely awful.

It was around midnight when her bedroom door finally opened, and Harold poked his head into his daughter's room. "I found out where he is, and they're letting us pick him up now instead of having to get him from the 'drunk tank' in five hours. Luckily he trashed one of his father's properties. So there won't be any charges pressed against him." He said, still sounding cheery. "So let's go get him before your mother wakes up and figures out what we're up to."

Blair was suddenly all too aware of the fact of how much she loved her father. She'd barely needed to explain the situation, and he'd figured it out in under two hours. Suddenly she saw where she got it from. She could only nod at her father before sneaking out of the penthouse with him.

"Did you and Nate break up?" He suddenly asked once they were in the town car, and heading to whatever precinct it was that Chuck was at.

She shook her head, and continued to stare out the window. "No, daddy. Why do you ask?"

Harold gave a low chuckle. "Just be careful with him, Blair-bear. I know he's been taking care of you since kindergarten-"

"He has not!" Blair all but screamed, sounding disgusted. "No one has been taking care of me. I take care of myself." Even as she said it, she had very distinct memories of elementary school flash through her mind. Like Hazel's dress being cut during a school assembly, and Serena magically getting food poisoning right before the class play in sixth grade, causing Blair, as the understudy, to have to play the part she'd memorized weeks before. Even the past couple of weeks that had propelled her to the queen of Constance popped through her mind. He really had been taking care of things for Blair since childhood, and it amazed her that her father noticed the things she didn't.

Her father patted her arm. "Just be careful. Things like this always get out of control. Especially with boys like Charles." He smiled warmly at her. "Just make sure you know what you're getting into."

As she stepped out of the town car, she couldn't help but to tell herself that she wasn't getting into anything; she was only getting Chuck out of a jam. After all, he'd do the same for her.

When they walked inside the precinct her eyes widened in horror when she saw the officer from the Queen's station. She immediately stalked over to the counter, leaving her father in the dust. "I thought you worked in Queens." She said dangerously low.

He laughed. "I was filling in over there." He glanced down at something before looking back up at Blair and grinning. "Let me guess. You're here to pick up Casanova again."

"Again?" Harold said as he appeared at Blair's shoulder.

She blushed as she stepped aside to let Harold pay the bail. "This may have happened a time or two before…" She admitted, not looking at her father.

"Bass!" She could hear faintly in the background a couple of minutes later. "Your girlfriend's here again!"

Blair could feel her father's eyes on her. She had the sudden urge to want to curl up and die. She also had the urge to lean against the counter again and try to hear what Chuck's reaction had been, but since her father was with her, she resisted that urge.

"Blair. We have. To stop. Meeting. Like this." Chuck drunkenly announced before stumbling over to her, wrapping his arms around her waist to keep from completely toppling over. In the process he nearly knocked her over. Instead of apologizing, he just laughed his drunken laugh again.

She wrinkled her nose at him. "You smell like a bar." She announced in disgust as she wrapped an arm around his waist and tried to get him to move towards the door. When he didn't move she looked helplessly at her father.

"Come along, Charles." Harold wrapped an arm around Chuck's shoulders and began steering him towards the door.

Chuck laughed when he realized who it was. "Mr. Waldorf!" He announced loudly and happily. "You. Have a beautiful daughter, sir. I don't know. What I'd do. Without Blair." He laughed his drunken laugh again.

Blair wanted to curl up and die. Especially when she walked past the officer from Queens, who merely grinned at her and said, "I thought he'd be your ex-boyfriend by now."

The car ride was the longest car ride of her life, and yet Blair was amused the entire time. She wasn't sure what was more entertaining: Chuck sticking his head out the window and screaming at the women on the street, or Chuck attempting to have a conversation with her father when he could barely talk. Still, although Chuck was entertaining, her father stared at her the entire time, and she couldn't help but feel like she'd been the one that committed the crime tonight.

She was completely surprised when they pulled up in front of their building. "Aren't we taking him to the Palace?" She asked her father in complete confusion as he started pulling Chuck out of the car.

Harold stared at her. "Like this?" He asked as he waved off the driver's help. "Let's get him upstairs."

Blair didn't know what to say to her father. She knew even less of what to say when they carried him to her room. Her father had just given her permission to hide Chuck Bass in her bedroom. Obviously, she had the most trusting father in the world.

Chuck glanced around the room, his hand on her desk to keep himself up right. "So that's your bed, huh?" He asked with a smirk, still capable of being pervy in his very drunken state.

"I should have ignored the phone calls…" She mumbled under her breath as she tried to figure out what she was going to do with him.

Before she could think of anything, Chuck suddenly disappeared into her bathroom and she heard him throwing up. It was odd to her to have someone other than her throwing up in her bathroom, and she wasn't sure how she felt about it. She didn't like just how similar she and Chuck were becoming in her mind.

She paced for about fifteen minutes before finally opening the bathroom door. A hand immediately went to her lips to stifle her laugh. There was the infamous Chuck Bass, lying on the floor of her bathroom with one of her very frilly towels pressed against his face. In the dark.

Rolling her eyes, she flipped the lights on and knelt down on the floor next to him. "Chuck?" She asked curiously as she pulled the towel away.

He groaned and looked up at her. "I think I shouldn't have had that last shot." He admitted sheepishly.

"Or maybe you shouldn't have had the last five shots you took." Blair offered as she pulled him up into a sitting position. "You're not going to throw up again, are you?"

He shook his head before flopping right back down onto the bathroom floor. "No. I think I'll sleep here though." He made a whiny sound. "I don't want to move."

Blair rolled her eyes at him as she let go of his arm. "And that's why you shouldn't drink on a Thursday."

Her towel hit her in the arm. "Why are you helping me?" He asked suddenly.

She shrugged. "You'd do the same for me."

Chuck laughed his drunk laugh again. "That's why I love you, Waldorf."

Suddenly Blair felt like she was the very drunk one. She was fairly certain she'd never heard Chuck use the 'L' word to describe anything in life. Oh yes, she knew she shouldn't have answered her phone tonight. "Wh-what did you say?" She stuttered out.

Drunk Chuck laughed again. "If I could love anyone in the world, it would be you."

She just stared at his drunk form as his eyes closed. "Why?" She whispered out, not knowing how she felt about this very drunk Chuck and the things he was telling her.

"You're just like me."

And then he passed out.

* * *

Xoxo

* * *

The first thing Blair was aware of when she awoke that morning was the arm sprawled across her stomach—the very male arm resting on her stomach. She blinked for a moment as she drowsily tried to remember why she was in her bed with a man. Then she remembered bailing Chuck Bass out of jail. Again. And the long night of taking care of his drunk ass.

Although he'd said he wasn't going to throw up again, he'd thrown up three more times throughout the night, and for some reason, she'd taken care of him. It was strange seeing Chuck so incapacitated that he needed to be taken care of, and that was the only reason she'd let him sleep in her bed with her. Well, that and it was easier to check on him, and he was too heavy to move to the floor.

She was contemplating how to wake him up and get him off her bed nicely when she suddenly felt his arm move. Sighing in relief, she sat up to make sure that he was okay.

"Waldorf?" Chuck asked in complete and utter confusion as he sat up and glanced around the room. "Am I in your bed?"

Blair groaned at his pervy smile, and knocked his arm the rest of the way off her stomach. "Yes, and trust me it won't happen again." She shot him a sickly sweet smile. "And I won't be bailing you of jail again, either."

He blinked for a moment as he studied her. "That was you, wasn't it…" He sounded thoughtful. "Was your father there?"

She couldn't hide her gleeful smile. "Yes." She said sweetly. "You confessed your undying love of me to him."

Chuck choked. "I'm sorry- What?" He stared at her in wide-eyed horror.

Blair giggled. "You're too easy sometimes."

He groaned and lay back on the bed, pulling one of her pillows over his face. "What time is it?" He muffled out.

"Just after nine. Daddy called the school and got us both out of class." Suddenly feeling exhausted again, she laid back down. "You can go home now, and that's not a suggestion."

A Chuck-like laugh escaped from underneath her pillow. "That requires moving, and your bed is comfortable." He paused for a moment. "Although, I do plan on testing out your bed later."

"You're disgusting." She announced with a half-hearted smack, too tired to actually argue with him that much. After all, she had spent the past eight hours taking care of his drunk ass.

Blair was so tired that she just let herself fall asleep again next to Chuck, and she was so tired that she didn't complain when Chuck's arm sprawled across her waist again. She was so tired that she actually _snuggled_ against him and let the sound of his breathing lull her back to sleep.

She never saw the Gossip Girl blast that read:

**Spotted: B and C both missing from classes today. Could it have anything to do with B leading C to her place at one in the morning? I wonder what N thinks now…**

And she never saw Nate come to the penthouse during lunch to check on her. She also didn't wake up to the picture Nate took of Blair asleep in Chuck's arms. And she thought that Nate didn't care about the Gossip Girl postings about her and Chuck. Unfortunately Blair was going to learn the hard way what her father meant when he'd warned her about getting herself involved in Chuck's world.


	3. Drug Possession

**Title**: Five Times Blair Bailed Chuck Out of Jail (and One Time She Didn't) [3/6]

**Disclaimer**: I don't own a thing.

**Author**: Diamondinsanity/karmawiccan

**Rating**: PG-13/T

**Pairing**: Chuck/Blair, Blair/Nate, Chuck/Hazel

**Spoilers**: None really.

**Timeline**: Pre-series. Sophomore year.

**Word Count**: 4324

**Summary**: Five times Blair has to bail Chuck out of jail, and one time they both have to be bailed out…

**Notes**: So… I'm a freak and noticed that in Blair's phone Chuck's name is just "Chuck," but in Chuck's phone Blair's name is "Blair Waldorf."

* * *

**XoXo**

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* * *

**

Much to Blair's surprise, waking up with Chuck Bass was beginning to become a habit. After taking care of his drunk ass three weeks ago, Blair had fallen asleep in the same bed as Chuck three times now. Once because they'd stayed up too late studying for a biology exam; Another time because she'd fallen asleep during some dumb movie Chuck made her watch; And then one time she'd just been too lazy to leave his suite and had passed out on his bed. Being friends with him was beginning to become a lot more natural than it had before, and she wasn't exactly sure how she felt about that. It seemed like the more times they bailed each other out of trouble, the closer they seemed to be getting.

The only weird part about the situation was that Gossip Girl wasn't commenting on her late night stayovers with Chuck. She wasn't sure how to feel about that. Once entering high school, she'd quickly learned that if Gossip Girl wasn't posting about you immediately, she was waiting for things to get even juicier. She kept hinting at it, mentioning that Constance St. Jude's had a new power couple, and showing pictures of her and Chuck at school, but there was nothing about their little sleepovers, and she was trying to figure out how she felt about that.

Despite the fact that he didn't like the term "power couple," Nate actually seemed to be enjoying the fact that she and Chuck were getting along so well. He said that it made his life easier, but Blair had a feeling that he wasn't quite giving his entire opinion about the whole situation. Still, he seemed more comfortable than he had since Serena left town. He'd even told her to let Chuck escort her to the Sophomore Caddyshack Extravaganza, since he had to go to some event with his parents.

Which was how Blair wound up on Chuck's bed flipping through his cell phone while he showered.

"Seven o'clock really means eight o'clock. Not nine, Chuck." She snapped loudly at him, knowing very well that he could still hear her. After all, he had conveniently left the bathroom door wide open after telling her that she was more than welcome to join him.

When he didn't respond, she shrugged and gave herself a once over in his mirror: Short white golf skirt, white polo, pale green headband, pale green knee socks, and white shoes. She looked like the perfect picture of a preppy country club girl. Or at least in the eighties sense which was the point of this mixer. When she was certain that her outfit couldn't get any more perfect, she turned her attentions to Chuck's bed, grinning when she saw his phone. It was time to get revenge for "Hot in Here."

She sat primly on his bed and grabbed his phone, making no haste in immediately searching for a brand new ring tone to surprise him with tonight. He'd embarrassed her with the ring tone he'd set for himself, it was her turn to return the favor. Laughing at the options she found, she quickly downloaded The Black Eyed Peas' "My Humps" and set that as his main ringer.

With that done and him still in the shower, she began lazily flipping through his phonebook. Her eyes widened when she saw that he had three-hundred and eighty numbers in his phone. She stared, wondering how he could possibly know that many people that well. Frowning, she began scrolling through the contacts.

Girl. Girl. Girl. Girl. Girl. Hooker (she had to be with a name like Sugar). Girl. Girl.

She rolled her eyes. Of course Chuck Bass would have a phone filled with only girl's names and numbers. He was Chuck Bass after all. She couldn't help but wonder how many of these women he'd actually called though. Probably less than half of them. She almost felt bad for the girls that thought they were going to actually get a second date with Chuck Bass.

When she got bored with looking through his list of whores, she went to his text messages, even though she knew she had to be wary here. She didn't want to accidentally read any of his dirty texts; she just wanted to know who he texted.

Nathaniel. Nathaniel. Nathaniel. Blair Waldorf. Nathaniel. Nathaniel.

She blinked at her name.

Blair Waldorf.

"That's not going to do."

Frowning she clicked on the 'edit contact' button, set on fixing her name so it only said Blair. Like he knew any other Blair's that were as important as she was. Or at least that was her intent until she saw that she was number four on his speed dial.

"Chuck!" She screamed as she stormed into his bathroom and propped herself up on the counter, glaring pointedly at the figure behind the contorted glass door.

He opened the door slightly, and poked his head out through the gap, giving Blair a once over. "And here I thought that you weren't going to take me up on my offer." A smirk lit up his face.

She rolled her eyes at him. "In your dreams, Bass." She crossed her legs as she avoided what she could see of his naked form. "I want to know why I'm only number four on your speed dial."

Silence lingered in the bathroom as he stared at her incredulously. He didn't say anything for a long while before suddenly rolling his eyes at her. "Don't you think there's a better time for this conversation?" He asked as he closed the door and continued on with his shower.

"No."

He groaned into the water. "Fine. If you must know, number one is my voicemail. Number two is Nathaniel. Number three is my father. And you are number four merely because you're the only girl I actually call more than once."

Blair couldn't help but to snort at that before suddenly frowning slightly. "Why is your voice mail number one?" That made no sense to her. Your best friend was supposed to be number one and then whoever you were dating was number two. That was how it worked.

"I get a lot of voicemails from numbers I don't know."

She rolled her eyes at him. "I'm sure you do." She looked down at the time on his cell phone before causally leaning over and flushing his toilet, listening to the curse words that poured from his mouth at the sudden temperature change. "Hurry up."

* * *

**XoXo**

**

* * *

**

"You look ridiculous." Blair declared when Chuck finally stepped out of his bathroom—fully clothed this time. Of course, he'd deemed it appropriate to come out of his bathroom completely nude the first time to retrieve his outfit. And of course Blair had been completely prepared with his cell phone, ready to take a picture and send it immediately to Gossip Girl. So Chuck had simply grabbed his clothes and hurried into his bathroom to finish getting ready while Blair tried to erase the image from her mind. It wasn't like she hadn't seen him naked before; he'd had to strip down to nothing in a game of truth or dare the year before. It really astounded her how she'd seen Chuck naked more than she'd seen her actual boyfriend naked. Two times more. Or three if she counted the glimpse she'd gotten when he was in the shower earlier.

Frowning at her comment, Chuck looked down at his outfit before glancing in the mirror to see if he was missing something. White tennis shoes he'd never actually worn before paired with equally new white tube socks, white pressed Bermuda shorts, a white polo and a pale green pullover sweater that accidentally matched Blair's socks and headbands. They seemed to accidentally do the matching thing a lot lately. He blinked, not seeing how he looked any more ridiculous than she did. Slowly he turned to face her. "And you don't?" He drawled out.

She let out a frustrated sigh at him before rolling her eyes. "Come on." She commanded as she grabbed his hand and began dragging him through his suite. "It's one thing to be fashionably late; it's quite another to be over an hour late. That's just trashy."

A frown slid onto Chuck's features as he grabbed a white coat, his cell phone, his wallet, and room key all while Blair dragged him out of his suite. "I always arrive an hour and a half late." He pointed out as he was led to the elevator.

"Like I said." Blair pressed the down button. "Trashy."

Chuck smirked. "If I'm so trashy, then while are you still holding my hand?" He asked with a wry smile and a cocked eyebrow.

Horror immediately washed through Blair. She glanced down as if that would prove that Chuck was making things up before realizing that he was completely serious and she had still been holding his hand. Quickly she let go of his hand, and all but ran into the elevator when it finally opened.

He laughed, and gave her a once over before following her into the elevator. "You look hot." The elevator doors closed. "Aren't you going to get cold in that though?"

"I'll be fine."

By the time the limo arrived at the mixer, Blair was wearing Chuck's jacket. She pointedly ignored his 'told you so' look as she checked his jacket under her name. Once that was done, they moved through the different groups of people, making sly comments about their outfits as they did so. When Blair got bored of that, she sent Chuck to "get her a drink" while she waited for the girls she was quickly turning into her followers—Serena's ex-followers. Like she predicted, the second Chuck disappeared, Hazel and Penelope arrived.

"No Nate tonight?" Penelope asked, sounding disappointed, but looking gleeful.

Blair shot her a sugary sweet smile. "Oh, no. He's at an important dinner meeting with his parents tonight." She made sure that each word oozed innocence.

Hazel shot her a very confused look. "But you always say that it's bad taste to show up at an event stag." She sounded very distraught about the whole thing.

Thankfully Blair felt Chuck approaching. It was hard not to sense him; his ego practically was a force field. She grinned brightly at the girls. "Oh, I never go any where without a date." She reminded them as Chuck handed her a drink. "You both know Chuck, right?" Again she made sure to sound as innocent as possible.

Chuck immediately took his cue and leered knowingly at Hazel. "Oh. Me and Hazel go real far back. Don't we, H?" He leaned closer to her. "Eighth grade, right? You gave me a hand."

Hazel stared at Chuck in complete and utter horror before stuttering out some sort of an excuse. She then stood there for a moment looking horrified. Then she ran away from them.

Once she was gone, Chuck gave an innocent shrug as Penelope stared at him like he was the most disgusting person in the world. "I was going to say that she gave me a hand with my English homework." He said nonchalantly. "I don't know how she could have taken that the wrong way…" He gave a knowing smirk.

Penelope gave Chuck a long hard once over before turning her attention back to Blair. "Being seen out with Chuck Bass is not the same as having a real date to an event, B." She sounded like she was the most important person in the room, and Blair hated that about her. "I'm sure if a girl in an even shorter skirt came along he'd go along with her instead."

Instinctively, Blair dug her nails into Chuck's arm to stop him from making some sort of comment to her taunt. She felt him flinch, and she vaguely wondered if she'd managed to break skin through his pullover. "Oh, did your date back out on you again?" Blair taunted back, sounding sweet about the whole thing. "That's harsh." She turned to Chuck, and slid the arm that had been attacking him through his. "Well, we have people we need to see. Later, P." She turned too sharply, and split her entire drink on Penelope. "Oops." She didn't sound sorry at all.

Once they were out of ear shot, Chuck slipped his arm out of her grasp and rubbed at it. "Do you know how to be gentle, Waldorf?" He snapped at her as he continued to baby his arm. "One day you're going to leave scars."

Blair scoffed at him and pushed him out onto the dance floor. "Oh, just shut up and dance with me." She commanded him.

A part of her should have known that this night was too good to be true. Everything was going perfectly. They'd managed to not only humiliate Hazel, but Penelope as well. She should have known that everything was going to go down hill fast.

"Can I cut in?"

Blair turned around in complete confusion at the voice. "Nate!" She squealed out happily, surprised to see him here. She'd thought he said that he wouldn't be able to come at all, but that didn't really matter to her. She was just happy that he was here.

When she turned around to tell Chuck that she was going to dance with Nate, he was no where to be found. It bothered her for a moment, but she merely shrugged and began dancing with her boyfriend. She honestly didn't think anything about Chuck's disappearance. Until she heard the shouting.

"Do I really look stupid enough to bring drugs to a school event?!"

Immediately Blair froze. "Chuck?" She whispered out, immediately detangling herself from Nate to see what was going on. In the back of her mind, she could hear Nate telling her to come back and grabbing at her hands, but she ignored him and pushed through the sudden crowd of students that had appeared. She felt herself freeze at the sight before her: there was Chuck being arrested in front of everyone in their class.

His eyes locked onto hers, and she could see the unasked question in his eyes. "You're going to bail me out, right?" She nodded immediately at the unspoken words, and made a phone motion with her hands to tell him to call her. After all, she needed to know where to pick him up from. His nod was the last thing she saw before the cops took him away.

Not a minute after he'd been taken away, phones started beeping every where.

**Spotted: C being taken to the big house for some serious amounts of fun in his jacket pocket. Who knew the letter C really stood for coke? **

Immediately Blair heard all the people around her gossiping about Chuck. She knew very well that Nate was talking to her and trying to get her to leave the mixer, but something about the text that gossip girl had sent out was bothering her. Frowning she read it one more time before she realized what it was. His jacket!

She turned to Nate, not wanting him to know about what she was going to do. "You know what? I was supposed to meet Kati and Iz ten minutes ago to tell them all about tonight since they both didn't want to come. I'm sure they'd love to hear all about this, and you hate girl talk. So I'll see you tomorrow?" She hoped she didn't sound like she was lying.

Nate merely nodded. "Yeah. I'm sure Chuck is probably going to be calling me asking me to get him soon any way." He kissed her cheek. "Tomorrow." He promised before disappearing out of the mixer.

Once she was certain he was gone, she took a long deep breath and sauntered over to the coat check. "Could I get my jacket? It's under Waldorf." She asked the girl, waiting impatiently to see if her theory was true. Sure enough, the girl handed Blair Chuck's white jacket.

Blair slipped it on, feeling slightly weird wearing his jacket while he was on his way to jail. "Hey, my date checked his jacket, too. I'm sure you know the one I'm talking about. He was kicked out earlier tonight. They didn't take his jacket with him, did they?" She asked, hoping that she sounded nonchalant about the whole thing.

The girl gave her a sad smile. "Sorry. They took it with them."

Pretending to be upset about it, Blair nodded slowly, and bit her lip. "You couldn't tell me what it looked like, could you? I think he borrowed one of my dad's and if daddy realizes that it's missing…" She let her voice trail off for a while before looking up at the girl again. "I could get into so much trouble."

The girl's sad smile suddenly turned into a pitying look. "Let me see if they took his slip." She said, trying to sound helpful. "What's his last name?"

"Bass." Blair supplied, suddenly feeling anxious.

The girl rummaged through a pile of slips for a moment before handing one to Blair. "There. A brown suede jacket."

Blair forced what she hoped was a relieved look on her face. "Oh thank God. It wasn't Daddy's." She slid the slip into Chuck's real jacket. "Thanks!" With that out of the way, she practically ran out of the mixer.

"Who would want to frame Chuck Bass?" She muttered to herself before taking a cab home to wait for Chuck's inevitable call.

* * *

**XoXo**

**

* * *

**

It was nearly four in the morning when Chuck finally called her. She'd given up on him calling; she'd even had a moment of weakness and threw on a tan Juicy sweat suit. Her lights had just been turned off and she climbing into her bed when all of a sudden she heard, "It's getting hot in here-"

Immediately she grabbed her phone. "What took you so long?" She snapped as a greeting.

He groaned on the other line, and Blair could have sworn that she heard him roll his eyes. "Well, I'm sorry I've been busy waiting for my lawyer, avoiding questions from the police, and trying to avoid expulsion." He snapped right back.

She sighed as she threw her hair into a ponytail. "Lawyer?" She asked, unable to hide the worry from her voice. "So, are you a free man already then?"

Chuck snorted. "Hardly. My father thought it would be a good lesson to have me spend the night in jail. Despite the fact that my lawyer managed to talk them out of the charges. Something about my resisting arrest…"

Blair was already out of her bed and was grabbing her bag. "Where are you at? I'm on my way." She took note of the precinct number he told her as she moved through the penthouse, not even caring at the moment if she awoke her parents.

"Thanks, Blair."

It sounded strange to her hearing Chuck Bass say thank you, and she wasn't exactly sure how she felt about it. Chuck Bass wasn't supposed to say thank you. He was supposed to be soulless and vile. It was really strange to her to hear him sound so… human.

"If someone framed me, you'd do the same." She said softly as she rode the elevator down, grinning when she recognized his silence as confusion. They really had been spending too much time together these days. "Besides, you're stupid, but you're not that stupid. And I had your jacket."

There was yelling in the background. "That's my cue. Apparently I'm out of time."

The line went dead.

"Why can't he just go a month without making me have to walk into a police station?" She mumbled under her breath as she climbed into a cab. The entire ride there she couldn't help but wonder who the hell would be stupid enough to frame him. Weren't people learning that you didn't mess with Chuck and Blair?

The first person whose name popped into her mind was Penelope, but she knew that Penelope wouldn't have the guts to do something like that. She seemed too sober to have pulled off a major scam. If it'd been her, she would have gotten drunk immediately to celebrate. She then thought that it might be Hazel, but despite the fact that Chuck had embarrassed her, Blair knew very well that Hazel had a crush on him and would never do anything that would ruin her chances with him again. After that, the list began to dwindle down to random people who didn't have any real grudges against Chuck. Idly she wondered if Nate would have any idea of who would want to do something like this to Chuck. Although she did have to admit, whoever did it was good.

She stormed into the police station and groaned when she saw the officer behind the counter. "You!" She accused as she stomped right up to him, unable to believe that every time she'd picked Chuck up, the same officer had been working. At three different precincts. "Do you not have a steady job, Officer-" Her eyes dropped to his name tag. "Morales?"

He chuckled, and it was obvious that he remembered her. "I fill in a lot." He said before dropping his eyes to his list. "Let me guess. Cassanova again?"

Already annoyed by the fact that she was bailing someone out who shouldn't have been arrested in the first place, she made a face at him before snapping, "Why do you call him that?" It made absolutely no sense to her.

Officer Morales just laughed again. "Let's just say that I've seen him arrested a lot, and we've learned not to move him past the ladies cell, or let him in a holding cell with anything that could be considered female." He paused for a moment, looking thoughtful. "Although… We did stick him and the Psycho he had with him a couple of weeks back in the same cell together, but we wanted to see if they'd kill each other…"

Blair couldn't help but to smile at that. Now that sounded like Chuck and Georgina.

"You have his bail?"

She nodded quickly, handed him her fake id and filled out all the forms she needed to fill out before handing out the cash that could have been spent on a new purse.

"I'll be right back."

Once Officer Morales disappeared, she leaned against the counter and waited for him to call Chuck. "Cassanova! Your girl's here!" The words were followed by the sound of the cell opening. "I don't know why that girl still puts up with you, boy."

"It's the sex."

Blair immediately rolled her eyes at Chuck's comment to the officer, and tapped her foot impatiently as she waited for him. "Finally!" She snapped when he appeared. "Let's go." She desperately wanted to discuss her list of possible framers with him.

"Hold your horses, Waldorf. I have to get my stuff first." He pointed out as he went over to the counter to get his belongings from Officer Morales. He took his cell phone, wallet and room key from him with out complaint, but shook his head at the brown suede jacket. "That's not mine." He sounded like he was reminding Morales of that fact, but he still took the jacket.

It felt like all the air had been drained from Blair's lungs. She knew very well whose jacket that was. After all, she'd been there when his mother had given it to him.

It was Nate's.

The entire cab ride she ignored anything that Chuck may have said to her and instead tried to wrap her mind around the fact that Chuck had been framed by his best friend. It made absolutely no sense to her. She really couldn't figure out why Nate would do something like that, but she didn't have the heart to ask Chuck. It was more than obvious that he had no idea this was Nate's jacket. Blair knew Chuck as well as she knew Nate. If Chuck had figured it out, he would be furious right now, and not laughing about how ridiculous the situation was.

When the cab started to go towards her place, she shook her head. "Can I stay with you tonight?" She didn't know why, but for some reason she didn't feel like sleeping alone tonight and she had a feeling it had to do with Nate.

Chuck merely stared at her.

"I'm not sleeping with you." She added on before redirecting the driver without waiting for Chuck to say yes or no. Of course he was going to say yes. She'd learned over the years that he didn't know how to say no to her.

He continued to stare at her. "You're the strangest girl I know, Waldorf."

* * *

**XoXo**

**

* * *

**

When Blair woke up the next morning, she was sprawled out in Chuck's bed with an arm thrown over his chest and her legs intertwined with his. Instinctively Blair checked to make sure she was still fully clothed before remembering the night before. She groaned. A part of her had hoped it'd been a nightmare, but seeing Chuck sleeping in his ridiculous outfit from the night before proved that it had all been real.

The only fact she'd been fuzzy on was why she had thought that spending the night with Chuck was a good answer to realizing her boyfriend had set up his best friend. It made absolutely no sense now, but she did have to admit that she'd slept remarkably well given the circumstances.

Deciding it was too early to even try to figure out last night any more, she closed her eyes again in an attempt to fall back asleep. That was when "My Humps" began playing.

Chuck groaned. "Waldorf, please tell me that is not my phone…"


	4. Assault

**Title**: Five Times Blair Bailed Chuck Out of Jail (and One Time She Didn't) [4/6]

**Author**: Diamondinsanity (lj) / karmawiccan (ff)

**Rating**: PG-13

**Pairings**: Chuck/Blair, Blair/Nate

**Timeline**: Pre-show/Sophomore year

**Word Count**: 5221

**Warnings/Spoilers**: None. Lots of foreshadowing though, considering this is set Sophomore year…

**Summary**: Five times Blair had to bail Chuck out of jail, and one time they both need to be bailed out.

**Notes**: Sorry this took so long. It is a decent-sized chapter though.

* * *

**X.O.X.O.**

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* * *

  
**

Blair Waldorf had always believed that she was living a real life fairytale. Everything in her life had been falling into place from a very young age. She had the perfect boyfriend, the perfect grades, and all the perfect connections she needed to get into Yale. Everything in her life was perfect. Until her stupid best friend had to run off to boarding school and leave her to deal with Nate and Chuck on her own. How could she? Didn't she know that the four of them only worked when they were all in the same city? Together they completed the elements of life. Without Serena they just weren't the same.

Serena was the earth. She might not always be in once piece, but she was there to hold everyone together. She'd always been the reason the four of them had become friends. She was the focal point. Nate was the air. His mind was always lost up in the clouds, but he was always there when you needed him to be. He took care of Serena when she was too drunk to take care of herself; he saved Chuck from destroying himself with his drug experimentations; and he was necessary for Blair's survival. She needed him to breathe. Chuck was the fire. He was rash, harsh, and destructive, but when you had fire to protect you from enemies, you didn't need much of anything else. He was the first one to fix every situation, and the one to make sure that whoever made you cry suffered a fiery death. And Blair? Well she knew very well that she was the water. She was cold and wrathful when she needed to be, but all it took was a little heat and she warmed right up. And she was the one that cleaned up Chuck's messes and made sure that Serena was still breathing.

They worked best as a unit of four, which was Blair's problem. Without Serena all they were fire, water, and air. Sure, water could put out fire, but air just gave it more fuel. She needed earth to balance things out. Otherwise she was going to get scorched. She could already feel the flames licking at her feet. A battle was brewing between Nate and Chuck and she didn't know how to stop it. She needed Serena.

Things had been rocky at best since the Caddyshack Extravaganza. Well… They were rocky between her and Nate. Things between her and Chuck were better than ever; sometimes he was a better best friend than Serena had been, but she still missed her. Serena would know how Nate thought, which would be helpful right now because she really was having a hard time believing that Nate would ever frame his best friend for drug possession. And yet the evidence was clearly there. Blair just needed to either figure out why Nate would ever do something like that. Or better yet, find proof that Nate didn't do it. After all, it did seem like a much more Georgina thing to do than a Nate thing.

Still, she needed to proof one way or another, which was why she was in Nate's room while he was out jogging with his father. It had been almost too easy. Ever since she was a little girl, she never could figure out why Anne Archibald always seemed to be oblivious to reality. It was like she lived in her own little drugged out world most of the time, which she wouldn't be surprised if Anne was drugged up on anxiety medicine. But it did help when Blair wanted to snoop on Nate. All she had to do was show up at the Archibalds', smile sweetly at Anne and mention something about needing to find something she left in Nate's room. Anne never seemed to think it was odd at all considering the fact that Blair liked to avoid Nate's place. She almost always made him come home with her after school to do homework. Anne really did weird her out.

The second Anne left her alone in Nate's room, Blair immediately began to rummage through Nate's belongings, careful to make sure to put everything back the way she'd found it. She opened every drawer that she could think off, and even rummaged through some of his books that looked very unread. But she didn't find anything. That was when her gaze landed upon his cell phone. Why he hadn't taken it with him was beyond her, but here it was, his cell phone. Shakily, she picked it up and went to his texts. When she saw that most of them were from her and Chuck, with the occasional text from Carter, she had a feeling that she would find anything in there. And she didn't want to know what Chuck and Nate talked about. It couldn't be anything good… So she casually flipped to his pictures. Her gaze immediately landed on the thumbnail of her in bed with Chuck. "Oh my effing God!"

And that was when her own cell phone started playing 'Hot in Here.' Nate's phone fell out of her fingers as she fumbled for her own. "What do you want?" She snapped at Chuck, making a point of keeping her voice low. Knowing her luck, Anne would have a moment of clarity for once and realize that it couldn't possibly be taking her this long just to find a headband.

"Well, hello to you, too, Waldorf." His smirk was even evident over the phone. "Bad time?"

She took a calming breath before hissing out. "Yes. So if you could call back in an hour…"

"I'll be quick." He promised. "The opening of Bart's newest hotel is tonight, and I'm expected to attend with a respectable date, and you're respectable-"

Footsteps were echoing closer to the door of Nate's room. "Yeah, fine, whatever." She said distractedly. "Call me back in an hour and we'll discuss outfit choices." And with that she hung up on Chuck Bass.

Hurriedly she picked up Nate's dropped cell phone, and quickly deleted the offending picture of her and Chuck before putting his cell phone back where she found it. She waited for the footsteps to get closer, and when they didn't, she figured it must have just been a maid. Sighing in relief, she slipped out of his room and all but ran down the stairs. She was down in the parlor collecting her jacket when she heard Nate's voice.

"Blair?" He sounded confused, like Anne he had a tendency to sound confused a lot. Maybe it was just a trait that ran in the family. Did all Vanderbilts sound confused all the time? She was going to have to investigate that…

She forced a smile on her face. "Nate!" She greeted sweetly as she pressed a kiss to his cheek. "I stopped by to catch up with your mother. It'd been a while since we had a real conversation." She really hoped that he wasn't aware of the fact that his mother made her uncomfortable.

"That was nice." He said slowly, sounding mostly convinced, but he still looked a little confused. "So we're still on for dinner tonight, right?"

She'd forgotten. "I'm sorry, Nate." And she really was. She didn't want to have to choose between Chuck and Nate; she really didn't, but she couldn't help but feel like that was all she'd been doing lately. This was why she needed Serena around. She needed her freaking earth! "I promised Chuck I'd go with him to that thing his dad's hosting tonight." She pressed another kiss to his cheek. "Tomorrow night. I promise." And with that she all but fled from the room.

* * *

**X.O.X.O.**

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**

"So explain to me exactly why you needed a respectable date?" Blair asked as Chuck guided her around the lobby of a midtown hotel that was nice, but not as nice as the Palace. It was a hotel designed for middle class tourists that of course would charge exuberant rates and always be flirting with full capacity, but it was middle class nevertheless. The other thing that annoyed her was the fact that they were the youngest people in the room. It was filled with middle-aged business men and their wives. Blair was bored to tears. The only amusing part of the entire situation was over hearing the wives murmur about what a cute couple they made. If they only knew…

Chuck didn't answer right away and instead lead her across the lobby. As they passed the mirror, Blair took the opportunity to glance at their reflections in the mirror. There they stood, her in a champagne colored cocktail dress, and him in a black suit and a matching champagne-colored bowtie. The gossiping middle-aged women were right—they did look good together. Blair quickly pushed that thought away and tried to focus on where Chuck was leading her. Finally, he stopped them just outside the entrance to the hotel's bar—a place that all the other guests seemed to be avoiding, which hadn't made sense to Blair, but apparently she was about to find out why.

"My father wants me to meet some members of the board tonight." He explained, studying her for a moment before continuing. "Apparently he thinks it'd be wise for me to meet them before I've finished at Princeton. Bart says it's important to be on good terms with them now just in case. As if he'd die prematurely. He's too stubborn for that." He gave an eye roll to emphasis the point that Bart dying young would never happen.

Blair however was still caught up on the fact that Chuck had invited her as his date to meet members of the board of Bass Enterprises. She knew there had to be some hidden agenda that he hadn't been telling her; there always was when it came to Chuck. "You want me to meet the board of Bass Enterprises?" She stared at him for a moment before the rest of his statement registered in her head. "And, what is this about Princeton? Serena is going to Brown. Nate is going to Dartmouth. You are coming to Yale with me so I know someone!"

He chose to ignore her comments and instead took her hand and led her into the bar, where Bart sat at a table with an older man and woman. "Father." He greeted as he led Blair over to the table.

Bart slowly stood up, lazily assessing Chuck and Blair for a moment before turning to the two board members. "Sylvia, Ronald." They both stood up at their respective names. "This is my son, Charles, and his-"

"Girlfriend." Blair supplied for him as she let go of Chuck's hand and instead moved to the two board members. "Blair Waldorf." She greeted as she shook both of their hands in turn before engaging both of them in conversation. Vaguely she could hear Bart excuse himself and Chuck, but she continued focused on her conversation as she attempted to eavesdrop on the other conversation in the room.

"Are you paying her?"

"What!"

"Blair."

"Sir, I can honestly tell you I wasn't expecting that."

"Charles…"

"What can I say? She likes telling people she's my girlfriend, and I have no idea why."

"Charles."

"Do you really think I could make something like that up?"

Blair grinned and continued on with her conversation. She didn't know why she did it; she honestly didn't. It just felt… natural. She blamed it on the fact that she'd been telling too many people that she was his girlfriend. Plus she had the added bonus of making Bart Bass uncomfortable, which was a rare occasion. The look on his face had been priceless. When they returned from their sidebar and joined into the conversation, she felt Chuck slide next to her, and slip his hand into hers. "Thank you." He whispered into her ear.

That was when she saw it, truly saw it: the look in his eyes, and she didn't know how to react to it. Maybe her father was right; she had let herself get too involved in this whole little scam with Chuck. She was beginning to confuse reality and their little world of lies. For a moment she'd actually forgotten that she wasn't Chuck's girlfriend.

* * *

**X.O.X.O.**

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**

An hour later, Chuck and Blair sat at the bar while Bart showed Sylvia and Ronald to their coats. They were having a celebratory drink. Blair couldn't believe it. They'd won over the members of the board. At first they seemed rather cold towards Chuck, but with Blair's help, they were eating out of the palm of his hand after fifteen minutes. Even Bart seemed impressed with the progress.

"It's all because of you." Chuck mumbled out as he swirled the scotch in his glass for a moment. She must have shot him a confused look because he continued on. "Ronald and Slyvia. They only liked me because you did." He took a long drink.

Blair just stared at him and waited for him to put the glass down before doing something completely and utterly unexpected. She leaned forward and gently pressed her lips against his; she blamed the three gin martinis she'd nursed. "You were amazing." She whispered out softly before leaning in to kiss him again.

That was when a voice cleared behind them. Immediately they both straightened up, guilty looks planted on both their faces as they turned to face Bart Bass. He was quiet for a long while, and just watched them. Blair suddenly realized why Chuck always went silent when his father looked at him so intensely; Bart Bass was a scary man.

"You did well tonight, son. There's hope for you yet." He said, finally, his eyes roving over to Blair, a knowing smile dancing in his eyes—the smile didn't make it to his mouth, just shone in his eyes. A look that said he knew very well that she hadn't been completely lying when she said she was Chuck's girlfriend. Her whole life she felt like she was stuck dating the both of them since they came as a pair, and now she couldn't help but feel like those words were truer now than they ever had been. And Bart Bass knew it. "I think I'll go talk to the other guests. Try and behave yourself, Charles." And with that he was gone.

Chuck stared at Blair for a long while. "I think we need more drinks." He motioned to the bartender.

Relief washed over Blair when she realized that Chuck wasn't going to mention the kiss, and she eagerly took the drink he offered her.

* * *

**X.O.X.O.**

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**

An hour later, Blair's arms were wrapped tightly around Chuck's waist as they staggered from his limo towards the Palace Hotel. She really couldn't believe that they'd hidden themselves away in a hotel bar while his father hosted a grand opening in the lobby and grand ballroom. Most of all she couldn't believe that she'd kissed Chuck Bass, and she couldn't believe that she was holding onto him so tightly. They stopped in front of the hotel, and Blair felt her back collide with the wall. A grin lit up her features as Chuck's lips hungrily pressed down against hers. The only thought in Blair's mind as she greedily kissed him back was that they'd both had way too much to drink.

She wasn't sure how long they were up against the front of the Palace making out, but she was very much aware of the fact that both her phone and Chuck's phone went off at the same time. Her mind was too clouded with alcohol, and too clouded with Chuck's natural musk that she wasn't aware of much of anything except his lips against hers, and the fact that his hand was on her thigh. There was a strange purring sound, and it took her a moment to realize that it was coming from her.

"Spend the night with me." He slurred the words into her ear, his lips pressed against the shell of her ear as he spoke.

Blair was about to do the most insane thing in her life, and actually agree when suddenly Chuck's weight went flying off her, and there stood Nate, looking angrier than she'd ever seen him as he drove his fist into Chuck's face. Suddenly Blair was completely and utterly sober as she watched in horror as Nate attacked Chuck again. "Nate! Stop it! Just stop it!" It didn't matter to her why Nate was here. The only thing she could really focus on was the fact that he was beating up his best friend because of her. She suddenly felt sick.

"I didn't need Gossip Girl to tell me. I already knew you were sleeping with her!" Nate screamed out as he pinned Chuck to the ground, his fist making a wet smacking sound as it collided again and again with Chuck's already bleeding face. "I knew there was something! That's why I tested you at the dance. She checked _your _coat under her name. Did you know that she always does that with me?"

Suddenly Chuck began fighting back, and Nate was pinned down on the sidewalk with Chuck on top of him, his fist pounding into Nate's face. "I'm not sleeping with your girlfriend!"

That was when Blair heard the sirens. She tried to yell at them to stop, and she tried pulling them apart, but there was nothing she could do. Nothing she could do but watch helplessly as the police put Chuck and Nate into separate cop cars and drove them away. There was nothing she could do until Bart came hurdling into the lobby, where Blair had chosen to wait for him.

"What did Chuck do?!" He immediately demanded to know.

That was when Blair was aware for the first time that there were tears streaming down her face. She couldn't believe it. Blair Waldorf did not cry in public, and yet here she was, tears streaming down her face as she shook her head wildly at Bart. "Chuck didn't do anything. Nate…" She wiped her tears away, not wanting to look up at Bart. "He attacked Chuck. And the cops-"

"I'm going to get him." Bart started across the lobby.

Immediately Blair was on her feet and taking larger than normal steps to catch up to him without running. "I'm coming with you." She announced.

"To hell you are."

Blair shot him a hard look. "I'm coming with you."

* * *

**X.O.X.O.**

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When they arrived at the precinct, Blair was out of the limo before it even stopped, and was inside before Bart could stop her. She flew into the building and straight for the counter where she knew Officer Morales would be. After all, he always just happened to be working whenever Chuck got arrested for something stupid. And, sure enough, there he was at the counter, and he didn't look surprised at all to see her.

"You're going to take me back there to see them now." She demanded the second she approached the counter. When he didn't say anything, Blair just shot him a look of pure annoyance. "See how my voice didn't go up at the end? It wasn't a question. You're taking me back there now!"

He looked weary for another minute before finally moving around and opening the door to let her into the back. "Just stay on the right side of the bars." He instructed as he let her back and took a hold of her elbow, guiding her to the holding cell. "And don't start another fight between them."

"I did not!" She defended.

Officer Morales scoffed at her. "Right, because 'Ruby Red' is a great shade of lipstick on Cassanova."

Blair did not dignify that with an answer. Instead she focused on the holding cell they were approaching. She immediately stopped and pressed a hand to Officer Morales' chest. "I'm fine from here, thanks." She snarked out. "You should probably go talk to Bart before he causes a scene." And with that she bounded over to the holding cell, a glare already firmly on her features.

She stared at the duo in the cell for a moment, noting that they'd been smart enough to keep both boys cuffed with their hands behind their backs. Well, at least they made up for being stupid enough to stick them in the same cell. Her gaze immediately was drawn to Chuck, who looked worse for the wear. He was sitting in the corner, his knees drawn up to his chest as he gazed at Nate in contempt. Despite the fact that his face looked awful, Blair had a feeling that his glare had nothing to do with what Nate had done to his face. This was all about the cocaine. She sighed slightly, and let her gaze land on his face, checking his damages. His left eye was already beginning to swell shut, there was a deep gash on his right cheek, and his lip was busted open. Yet, Officer Morales had been right; she could still see her lipstick on his face.

Her gaze moved from Chuck to Nate, who sat on the far opposite side of the cell. It was as though he didn't want to be anywhere close to Chuck, which was probably an accurate assumption. He didn't look angry though; he looked smug. She shook her head before taking in Nate's injuries. Even though Chuck didn't have as long to throw punches as Nate did, he'd gotten some good punches in. Nate's black eye was already forming, and it looked like Chuck had broken his nose.

Rolling her eyes at the sight they both made, she composed herself before stalking right up to the bars of the holding cell they were thankfully sharing alone. "Well, aren't you both just an eyesore." She announced as she tried to appear casual and act as though their faces didn't bother her. "So were either of you planning on telling me that you joined Fight Club?"

Instantly both boys were on their feet and approaching the bars, hopeful looks on both their faces. Immediately Blair understood. They wanted to see who she was here to fetch; who she was going to choose. Were they really serious? They wanted her to choose between her best friend, who'd she'd been caught making out with, and her boyfriend, who planted cocaine in his best friend's jacket? Clearly they were both insane if they really thought she was going to choose.

Before either of them could even speak, she had her hands up to silence them. "No." She turned to Nate. "I am not sleeping with him." She smiled sweetly. "And, honey, it's never a good idea to leave your cell phone unattended." With that, she turned her attention to Chuck. "And you! You broke my boyfriend's nose! There's no way I can take him to my mother's dinner next week! And you look even worse than he does! Who the hell am I supposed to bring as a date now!?" She composed herself for a moment before making her gaze steely again. "And for the record? I'm not speaking to either of you until you sort out your problems." With that, she turned on her heel and began to leave.

"Blair!"

She wasn't sure who said her name first, but she stopped regardless and slowly turned to face them again. "No." She made sure her gaze was fixed on Chuck. "I'm not bailing you out. Have a fun sleepover, boys!" And with that she flounced back out to the front of the station, a grin firmly planted on her features as she sidled up towards Bart, who did not look happy at all to see her. "Give them a couple of minutes to think that they're both spending the night. A bit of torture will do them both good." She shot Bart a dazzling smile. "I'll be in the limo getting the ice ready."

The smile wouldn't shake from her features as she climbed into the back of the limo, and started putting ice into a glass to press against Chuck's face. She knew very well that Bart would make sure that Nate spent the night in jail. No one attacked a Bass and got away with it. That was just the way it was. And did Blair feel bad knowing that her boyfriend would be spending the night behind bars? Not really, and that worried her more than she was willing to admit.

"Waldorf!" Chuck greeted in pleasant surprise, still sounding slightly drunk as he climbed into the limo, and promptly dropped himself next to Blair, his head resting in her lap. "And here I thought you were mad at me for ruining Mommy's dinner." He smirked up at her. "Does this mean you'll be playing nurse?"

Blair smiled sweetly at him before pinching his cut cheek.

"Fuck Waldorf!" He bellowed, jumping into a sitting position as his father merely shook his head at the teenagers' antics, and instructed the driver to take them back to the Palace. The motion of the limo suddenly moving was enough to knock Chuck right back into Blair's lap.

Her sweet smile didn't falter. "Oh, stop being a baby." She placed a hand on his shoulder so he wouldn't move again before pressing the glass of ice against his bloodied cheek and lip. "What are you going to do when the doctor stitches your face up? Scream like a little girl?" Her voice turned as sickly sweet as her smile. "I'll give you a treat if you're a good boy."

Bart reacted at this. "Dr. Barnes said it would take at least a half hour to arrive. I'm sure you can find something to tie him to in the meantime." He chipped in, a small smile appearing at the look of horror on his son's face.

"I can't believe you're ganging up on me!" Chuck whined out.

Blair's grin turned into a real smile. "Aw, is Chuckles afraid of the doctor?" She asked playfully, her smile brightening when he flinched beneath her. "Don't worry, I'll protect you."

He scoffed at that. "Oh yeah. You'll protect me alright." He glared up at her, not making a move to get out of her lap, even when they quickly arrived at the Palace. "You'll help him shove scalpels into my face."

"Oh. Not scalpels." She grinned wickedly down at him. "Needles."

* * *

**X.O.X.O.**

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By the time Dr. Barnes arrived, Bart was no where to be seen, and Blair was in Chuck's suite, curled up in the bed with him, pressing an ice pack against his face, which seemed to be distracting him enough to refrain from thinking about locking his door so the doctor couldn't come in. But come in he did, and Blair realized why Chuck had been whining in the limo. He really was afraid of doctors. Once the doctor was in the room, and took the ice pack away from Blair, Chuck's legs were suddenly intertwined with Blair's, effectively keeping her from abandoning him on the bed. When the needle and dissolving thread were pulled out, Chuck's hand suddenly found her arm, and Blair felt like he was clutching at her for dear life.

That was when Blair made her final mistake for the night, and pressed her hand against his. "You don't have to do this if you really don't want to, Bass. I'm sure you could make an unsightly scar work for you."

He just looked at her, and didn't say a word.

"Are you sure?" She prompted.

His lips pressed against her shoulder in response.

Blair looked at the doctor. "Sew away."

When the doctor was done, Blair knew that she was going to have bruises on her arm from where Chuck clung, but she figured she deserved it. After all, both Chuck and Nate were covered in bruises and cuts, and considering it was all her fault, she figured she might as well sport war wounds as well. It was only fair.

They lay in bed a long while without talking. They lay there so long that Blair was convinced that Chuck had fallen asleep. Taking her opportunity to leave, she started to slip out of the bed, but Chuck's fingers laced around her wrist before she'd barely sat up. "Stay." His voice was soft and it was more than obvious that he'd been thinking about what happened.

She nodded slowly, and lay back down, this time with her head barely touching his shoulder.

"I thought you weren't taking sides." He said finally.

Blair didn't dare look at him. Instead, she just moved her head further onto his shoulder out of hopes that it would distract him. When his gaze stayed on her, Blair made a noncommittal sound. "We're Chuck and Blair." She said finally. "You get sent to jail, and I bail you out. That's what we do."

That answer seemed to work for him because he reached over and turned his lamp off, surrounding them in darkness. His hands didn't roam anywhere inappropriately, he just wrapped an arm around Blair's shoulders, and didn't say a word after that. He didn't need to. Blair knew him well enough to know that he was processing what she'd just said in regards to what happened that night. Over-thinking was his specialty and she left him to his thoughts as she thought about what she was going to do.

She really did miss Serena. If Serena had stayed, this wouldn't have happened. If Serena had stayed, she wouldn't be spending all her time with Chuck. If Serena had stayed, Blair's world wouldn't be such a mess. She really did need Serena. Without earth, there was nothing to keep the other three grounded. Fire and water went hand in hand with each other. They complimented each other. But air? It really didn't have a purpose without the earth, and that terrified Blair. It terrified Blair that without Serena she didn't have any real motivation to spend time with her boyfriend.

It was that thought that haunted her long after Chuck had fallen asleep, and it was that thought that haunted her dreams.

* * *

**X.O.X.O.**

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When Blair first awoke, it took her a moment to realize where she was. It wasn't until she saw Chuck's arm sprawled across her stomach and felt his legs intertwined with hers that she realized that she'd spent the night at Chuck's. Again. She was contemplating leaving when she heard Bart out in the front of the room yelling at someone. Instinctively, her eyes flew shut again and she pretended to still be asleep as she eavesdropped on the conversation.

"No. You will not be changing his sheets." He instructed housekeeping. "You will do as I originally told you to and have breakfast brought up to my son and his girlfriend."

Blair groaned and buried her face back into Chuck's shoulder. Her father had been right. She let herself get in over her head. It was that moment when she realized for the first time that she'd chosen Chuck over Nate. For the first time in her life, she'd taken sides and had chosen Chuck. What the hell was she going to do now?


	5. Solicitation

**Title:** Five Times Blair Bailed Chuck Out of Jail (And One Time She Didn't) [5/6]

**Author:** Diamondinsanity (lj) / Karmawiccan (ff)

**Rating:** PG-13

**Timeline:** Pre-Show/ Sophomore year

**Pairings:** Chuck/Blair, Blair/Nate

**Summary:** Five times Blair bailed Chuck out of jail and one time they both needed to be bailed out

**Word Count:** 5676

**Notes:** I miss fluffy!Chuck/Blair. I miss the Chuck who used to laugh and make fun of everyone. I like the Chuck who used to say things like "What? The Captain's dislike of starchy shirts, I totally sympathize. The collars chaff." That is the Chuck I like, and due to his sudden re-emergence at prom, I suddenly felt inspired again. Here's hoping to a fluffy finale.

**Notes 2:** This is not an AU fic. It's just a preseries fic. Just so you know.

**Notes 3:** Alright, this is NOT the final chapter. One more to go, peoples, and don't even worry. It's half written and should be up in a couple of days. I'm determined to have it finished before the finale.

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**X.O.X.O.**

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"Your face is almost back to normal." Blair snapped as she leaned back against the pillows of her bed and studied Chuck as he stared at his face in her vanity's mirror. "Aren't you supposed to be here comforting me and not just staring at the mirror and trying to figure out if you need a nose job?"

That got Chuck's attention, and he slowly turned away from the mirror to look at Blair. "And you also invited me over here on false pretenses." He pointed out lazily. "You said Harold was moving out."

Blair shot him a glare as she sat up to look at him better. "He is moving out."

"Yes." He nodded in mock understanding. "I understand the fact he's eventually moving out, but that does not warrant a six am phone call."

Immediately, Blair regretted calling him. Obviously he didn't understand what she was going through. "He's leaving my mother for another man!" She tried to justify. God, she missed Serena. She would understand.

Chuck nodded again. "So I heard. Roman, right?" He waited until she nodded in confirmation before continuing on. "I completely understand. He's not bad looking." Despite Blair's dirty look, he continued on. "It's all about upgrading when you hit Harold's age. Roman is definitely an upgrade."

"Ugh!" Blair threw one of her pillows at Chuck's head. "You're heinous."

He turned his attention back to the mirror. "No. I'm Chuck." When she didn't say anything, he glanced at her in the mirror. "As opposed to being Serena. I don't quite fill her Jimmy Choo's, don't you think?"

Blair grumbled something unintelligible, hating when Chuck was right. That was one of the major flaws in their relationship. She would much rather that she was always right. A groan escaped her lips when she realized that she'd referred to this _thing_ with Chuck as a relationship, which as far as their parents assumed, they were in a relationship. Blair really didn't know what to call it, or what to think about it, so she chose not to. Instead she thought about what Chuck had said about her father and Roman. "Oh. My. God." She whispered out suddenly.

Index finger still on his nose as he reassured himself that there was no unnatural bump there as Blair had insinuated, Chuck turned away from the mirror at her gasped out words and instead focused his attention onto Blair. "What?" He asked, still sounding lazy.

"You're my father!"

Chuck raised an eyebrow at that and let his hand fall. "Excuse me?" He asked, not completely understanding. "I'm your father?" He repeated in an attempt to figure out where Blair was going with this before throwing Blair's pillow back at her when he understood part of the implication of her words. "You think I'd actually get married to someone one day? That's insulting, Waldorf!"

She rolled her eyes, not surprised that Chuck wasn't following what she was trying to tell him. That seemed to be the pattern of this morning. "No, not that part." She started before frowning lightly as she thought about. "Well… Kind of that part. You're my father." She started again.

"I get that." Chuck sounded just as exasperated as she felt. "What I don't understand is why I'm your father. Do you make out with your father on a frequent basis, Waldorf?"

Blair made a face at him. "You'd like that wouldn't you, Basshole. No." She took a calming breath before explaining what she meant to him as though he were a young child. "You and Daddy have the same personality. That's why you get along so well. You're going to leave your future wife for a man or however your whole upgrading thing works."

There was a long pause as Chuck just stared at her for a moment before he suddenly shook his head at her. "It amazes me that you think I'm stupid enough to get married." He pointed out before suddenly getting up. "Let's go to breakfast."

Sometimes Blair didn't understand the way that Chuck's mind worked. "You want to go to breakfast?" She asked him slowly before sighing exasperatedly when he nodded. "Fine. Let me change."

Chuck didn't leave.

"Chuck!"

He smiled sweetly at her as she climbed out of her bed in her dressing gown. "What?" He asked innocently.

"Get out!"

His innocent smile turned into a smirk. "No need to be shy, Waldorf. It's not like it's nothing I haven't felt up before." He smarmed out.

Blair huffed and began shoving him out of her room and directly into Harold.

"Good morning, Mr. Waldorf." Chuck smiled out as though it were a completely normal situation.

Harold, for his part, did not seem to be fazed at all by the fact that Chuck was in Blair's room at seven thirty in the morning. "Stay over again, Charles?" He asked with a warm smile.

An annoyed sound spewed from Blair's lips at how chummy her father and Chuck were before she slammed her door and stomped around in her room, looking for something to wear to breakfast. She didn't understand why her father and Chuck had always gotten along so well, but her theory made complete and utter sense to her. They were both too similar for their own good. They even both liked wearing ridiculous outfits.

As Blair pulled on an outfit, she froze when she thought about that old saying that girls always married men just like their fathers, but quickly shook that thought away as she pulled her shoes on. "Chuck doesn't even want to get married." She reminded herself as she sat down at her vanity and quickly put some makeup on. "Who doesn't want to get married? That's ridiculous." She continued talking to herself as she made herself somewhat presentable. When she was certain that she looked good enough to go out into public, she stepped out into the hallway, expecting to find Chuck and her father, but they were no where in sight.

"Daddy?" She called out in confusion as she walked down the hallway, not liking the fact that they'd disappeared together. "Chuck?" She tried again to no avail. Frowning, she started down the stairs, wondering if they were down in the living room. She hadn't taken _that_ long getting ready. Suddenly a dark thought popped into her head and her eyes widened in horror. "My father is trying to seduce my pseudo boyfriend."

As she descended the stairs, she froze at the sight before her in the living room. There was her father standing in the living room talking to Chuck and Roman. For a second Blair was certain that she must have smoked a joint with Chuck and now was very very high, but her father's pleasant smile, and the almost guilty looking expression on Chuck's face immediately dashed those hopes. Chuck really was having a conversation with her father and her father's boyfriend in her mother's house. Something really wasn't right here.

Before anyone else could react to her appearance, Chuck was at the bottom of the stairs and taking her by the elbow to guide her the rest of the way into the living room. Normal people would have just thought that he was being gentlemanly, but Blair knew him too well to be anywhere stupid enough to believe something like. Chuck always had a motive behind everything that he did. "Your mother apparently left early this morning for a Botox appointment." There was humor in his voice at that. "Oh, and-"

But Blair never got to know what the other part was because her father started talking, successfully cutting Chuck off. "Charles! Don't ruin the surprise before I can tell her." Harold scolded, obviously knowing as well as Blair did that Chuck had a motive behind everything. "We're going out to breakfast."

Off Blair's look, Chuck sent her an amused look. "All four of us." He explained, doing his best not to show how much the situation really amused him.

"A double date." Roman supplied.

Blair stared at Chuck in utter and absolute horror. "I hate you." She hissed into his ear, convinced that he was somehow responsible for this piece of horror.

Chuck smirked. "Don't lie to yourself, Waldorf. You love me." He smarmed out.

She made a face at him, but before she could say anything to the contrary in front of her father, Chuck completely distracted her by slipping his hand into hers. All she could do was stare at him. Blair and Chuck holding hands. Who could have ever imagined that? She certainly was still having a problem grasping it, and yet, when she told her parents that she'd had a fight with Nate the week before, they had both assumed it had been because of Chuck. Apparently everyone else was fine with the fact that she was "dating" Chuck. Stupid Bart and his big mouth. She knew very well that Bart had tipped off her parents to the fact that she'd introduced herself as his girlfriend. Now she just had to figure out how to get revenge on Chuck's father. It was all his fault she was now being forced on a double breakfast date with Chuck, her father and her father's boyfriend. It was like the plot of a _Lifetime_ movie gone wrong.

"Shall we go then, Harold?" Chuck asked in that sickenly charming voice he used when talking to adults he wanted to impress and then they were off on the double date from hell.

* * *

**X****.O.X.O.**

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For once in her life, Blair Waldorf was at a loss for words. She liked to think that she'd been perfectly coifed and groomed to be a society women; she used to think that no matter the situation she would be able to control the conversation, but none of her classes had ever prepared her for this. Her father was talking about **hockey** with Chuck. Harold Waldorf and Chuck Bass were talking about HOCKEY! She didn't even know that either of them liked hockey, and here they were having an in-depth conversation about it. Even Roman seemed to know enough about it to toss in a couple of points. Blair was at a complete and utter loss. Who knew that men liked hockey?

She poked lazily at her eggs Benedict, not even bothering to pay attention to the conversation any more. After all, what was the point? All of this was just too weird for her to wrap her head around. Her father and Chuck got along as though they were old friends. Her parents' marriage was over. Her father was moving away with another man. Her mother was getting Botox. For once in her life, she wasn't seeing Nate. It was all too weird and too much for her to handle.

"You alright, Waldorf?"

She suddenly looked away from her eggs and found herself staring at Chuck. Immediately she looked away from him and glanced at the other side of the table only to find that they were now alone at the table. "Where's Daddy and Roman?" She asked, sounding more tired than she would have liked.

"They went to pay the bill. Secretly, I think they wanted a drink before heading back to the penthouse and didn't want us to see." He shrugged lightly. "I don't know where this stigma about drinking before noon comes from…"

She nodded slowly before getting up. "I'm going to the ladies room." It wasn't a lie. She needed to get the hell out of here and away from her weird thoughts and the bathroom was the only place she could escape to.

Chuck's hand latched around her wrist. "Blair." His voice had a warning quality to it, as if he knew exactly what she was going to do.

"Let go of me." She pressed her lips together.

"Blair."

She sighed. "It's weird. Since when are you and Daddy best friends?" She snapped out, not caring that a couple of patrons were staring at them now. "Did you know that he doesn't even like Nate? Why does he like you so much?"

This time Chuck sighed. "Blair," He tried again.

"No. It's weird enough that our parents think we're dating. It's too much that Daddy likes you more than my actual boyfriend."

His face darkened at that. "And here I was under the impression that you were avoiding any form of communication with Nathaniel." His grip on her wrist tightened. "Funny. Didn't you tell him that you were done choosing sides only to choose my side?"

Blair fought back the urge to slap Chuck in front of such a large audience. Instead she just took a deep breath. "Let go of my arm, Chuck." She hissed out.

He studied her for a moment before suddenly shooting her a sickly sweet look. "Sure thing, Princess."

Once her arm was free from his grasp, she all but ran to the bathroom. She locked herself in the first stall and threw herself onto the ground, a part of her hoping that she'd have bruises tomorrow. Once again, she let all of her confusing thoughts about the twisted tangle her life had become overwhelm her and forced herself to throw up her half-eaten breakfast. When she was done, she sat on the floor of the bathroom for a couple of minutes before regaining her composure, flushing the toilet and walking out to the sinks to wash her mouth out. She reapplied her lipstick and made sure her hair still looked alright before stepping out of the ladies' room.

Chuck leaned against the wall, obviously waiting for her. He didn't say a word, even though by the look on his face, he knew exactly what she'd been doing. Instead, he just took her arm and started leading her out of the restaurant. He waited until they were almost to the door before saying anything. "Harold and Roman are waiting by the car. I told them you wanted to freshen up. I'm fairly certain they think we're having sex." He shot her a sideways look. "Maybe we should muss up your hair a bit."

"Try it and die." She told him, unable to hide the wide smile that was now on her face. It didn't matter if they fought, or if her bulimia was worse than normal, they were still them. Chuck and Blair. They fought and made up and Blair wouldn't have it any other way. Although, she could do without her father thinking that she would have sex with Chuck in a public restaurant.

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**X****.O.X.O.**

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**

Blair sat in her room later that evening thinking once again about what her life was coming to. She really didn't know what she was going to do without her father in her life. It wasn't like her mother was a good influence in her life. In fact, she tended to just make a lot of things worse. Eleanor didn't approve of anything she wore, or even a lot of the things she did for that matter. It was hard having a mother who only seemed to care when it was negatively based. Her father always balanced her out. He was the supportive one while she was the critical one. Blair didn't know how she was going to survive life with just her mother. Everyone who used to save her from her was gone: her father was leaving, Serena was at boarding school, and she'd pushed Nate away. The only person she had left was Chuck, and he was sometimes worse than her mother. Eleanor didn't see anything; but Chuck saw it all. She really didn't know what she was going to do now.

She sighed as she threw herself down on her bed, contemplating watching _Breakfast at Tiffany's. _It always made her feel better, but it also made her think of Serena, and that was the last thing she wanted to do at the moment. All she really wanted was just to forget all about this tangled mess she'd managed to get herself in.

"Oh, no you don't."

Immediately Blair shot up into a sitting position at the sound of Chuck's voice. She looked at him in horror for a moment before immediately playing with her hair, in an attempt to make sure that she actually looked presentable. Dorota was supposed to warn her when guests were coming into her room, and now she was going to have to yell at her. "What are you doing in here, Bass?" She snapped out.

Chuck merely grinned at her. "We're going out." He declared as closed the distance between them and grabbed her hand. "Right now." And with that he started dragging her out of her bedroom.

"No." She pouted defiantly at him as she attempted to dig her heels into the floor.

"Yes." He continued dragging her out of the room.

"No."

"Yes."

Finally, Blair sighed in desperation. "Fine." She knew that when Chuck got something into his head, there was no real way to talk him out of it. "But I'm changing." She then slipped her wrist out of his grasp and pushed him out of her room for the second time that day.

"Wear something hot!" He shouted through the door. "There's this club I want to take you to." Once she made a huffing sound, he added on, "I'm going to go talk to Harold."

Blair stayed by her door for a moment, waiting for the inevitable sound of Chuck moving away from the door and the sound of her father's study opening before finally running over to her closet to find something to wear. She stared into her closet for a moment, contemplating what to wear. For a brief moment she thought about wearing one of her mother's pieces, just to spite him, since he liked to lament that her mother was a horrible designer, but she couldn't help but want to do what he said. She spied a red slinky dress that she hadn't had any opportunity to wear yet and decided to try it on.

Blinking slightly at her reflection in the mirror, Blair tilted her head to the side as she stared at herself. It was cut a lot higher than she'd prefer to wear and she hadn't noticed that there was a slit in the back. She bit her lip slightly as she thought about changing. It wasn't something a Waldorf would wear; it was something a van der Woodsen would wear which was why she'd bought it. At the time, she'd wanted to be like Serena, and now she just felt like a floozy. Still, regardless of that thought, she pulled out a pair of matching shoes to see if it would make the outfit look any less skanky. She bit her lip again and immediately decided that she should change. That was when her door opened.

"Wal----dorf." Chuck gave a low whistle as he surveyed her form. "That's more like it." Without waiting for her to explain that this wasn't her real outfit, he grabbed her hand and began dragging her out of the penthouse. She'd barely had time to grab her purse, let alone to stop him from dragging her out of her own house when she was dressed in something Serena would pull off better than she could.

* * *

**X.O.X.O.**

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* * *

  
**

Sometimes Blair couldn't help but to forget that Chuck didn't party like the rest of the Upper East Side did; he liked slumming it. Sure, it was something she liked teasing him about, but she hadn't actually thought that he would ever attempt to take her to one of his skanky downtown clubs, and yet here they were at some strip club.

"I am not going in there." She announced, crossing her arms over her chest.

Chuck rolled his eyes, and grabbed her hand, their fingers interlocking as though it were completely normal, and Blair found herself wondering when it had become normal. "Trust me, Waldorf. Would I ever steer you to a bad place to party? Please." And with that, he dragged her into the club.

As they passed through the scantily clad people, Blair couldn't help but to wonder if this is what her life was going to turn into. Now that she had chosen Chuck over Nate would this be the type of things that she would do? Would she go out every night of the week and party like the middle class did? Would she become just another one of Chuck's many whores? She really didn't want to think about it. Now that she'd chosen sides, she wasn't exactly sure if she'd made the right choice.

When Chuck offered to get them drinks, she'd never been so happy to ask for a gin martini in her life. She was going to need alcohol in her if this really was the place that he'd wanted to take her to, and here she'd used to think that Chuck had decent taste. Her gaze passed over all the people on the dance floor and up to the dancers on stage. For one brief moment she wondered if Chuck had ever taken Nate here. Had he taken her boyfriend to a place where women took their clothes off for money? Then, she found herself thinking how freeing it must be to just take everything off and let everyone just see the real you. It seemed like it would be refreshing.

Quickly Blair shook that thought out of her head and pressed a hand to her forehead, thinking that she really had spent way too much time with Chuck these past couple of weeks. Like she would ever actually become a stripper… With another shake of her head, she turned away from the stage and moved through the crowd, determined to find Chuck. She really needed to be drunk right now. When she found him, she immediately took the drink out of his hand and downed it.

"Another one."

Chuck raised an eyebrow at her. "Starting the night off strong, are we, Waldorf?" He looked amused, but there was something else in his gaze that Blair couldn't quite figure out.

"Just get me another drink." She demanded. "I'm going to dance."

Without waiting for him to respond to that she slipped out onto the dance floor amidst the throes of people. As she glanced around she realized that this place wasn't like the strip clubs she'd seen in movies. Sure, there were strippers on the stage, but that was really it. The rest of the club was filled with both men and women drinking and having a good time. No one was sticking dollar bills down anyone's g-string. It was… classy. It was then that she realized that she might not mind living this lifestyle with Chuck and that frightened her a bit. He wasn't the happily ever after that she'd imagined as a young child.

All her thoughts got pushed away when he suddenly appeared next to her on the dance floor and handed her another martini. It looked like he wanted to say something to her, but it was at that precise moment that someone shoved into her and she found herself pressed up against Chuck's chest. She looked at him, and he looked right back at her, but neither of them actually said anything. Blair just grinned, and did the first thing that came to her mind. She leaned up and pressed a quick kiss to his lips.

"Thank you!" She shouted over the music at him.

He raised an eyebrow at her before taking a sip of what was probably scotch. "For what?"

Blair shrugged. "For today." She suddenly felt embarrassed for everything, and decided to take a very large sip of her drink.

Chuck didn't say anything to that, he just took her hand and led her away from the dance floor and into a small alcove not far from the stage. He settled into the loveseat there, and waited for her to do the same. That was when their cell phones both started going off in unison. He looked at her as if asking her if she really wanted to look at Gossip Girl after everything she'd learned about her parents the day before.

It was weird for Blair to see Chuck actually look concerned for her well-being, but she dismissed the thought and opened her phone.

**Spotted: B and C lovin' on the dance floor, and here we thought that Queen B didn't go downtown…**

Chuck hadn't even bothered opening his phone. He just looked at her waiting for her reaction. "Should I get more drinks?" When Blair didn't say anything, just looked at the pictures, Chuck nodded. "I'll get more drinks."

* * *

**X.O.X.O.**

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* * *

  
**

Blair had no idea how much she'd had to drink now, but she knew one thing. She was far too drunk for her own good. That was her only explanation for her current predicament. Otherwise she had no idea how to explain to anyone why she was alone in an alcove in a classy strip club with Chuck Bass straddling his lap.

His hands slipped up her thighs, toying with the red fabric that barely covered her form. Grinning against her flesh, he pressed kisses across her collarbone before slowly kissing up her neck. He nibbled on her earlobe for a moment before asking in a low husky voice, "Have I told you how hot you look tonight?"

Unable to think of any other response, she giggled and kissed him again. For a brief moment she tried to think how long they'd been in this alcove, and just what had led her to start kissing him again, but she couldn't remember. All she knew was that for some reason she couldn't fathom, it made complete and utter sense to her. This was the way it was supposed to be.

She pulled away from his mouth and instead gently bit his neck. When he shuddered lightly beneath him, she could only grin and do it again.

Suddenly, Chuck pulled her slightly away from him, and tucked a loose strand of hair behind her ear. "Come home with me tonight." He said seriously, as if being serious would make it perfectly clear to her what would happen if she came home with him tonight.

"I just need to go to the bathroom to freshen up first." She didn't know why she was saying it; she really didn't. It must have been because of the alcohol. That was the only excuse she could think of as to why she was seriously considering giving Chuck Bass her virginity.

A grin suddenly filled Chuck's face, and he pulled her close to him, kissing her desperately once again.

Laughing, Blair slipped out of his grasp. "Meet me outside in five minutes." She instructed him before pushing through all the people and to the bathroom. Once she was inside, she stared at her reflection in the mirror. For a second she didn't quite even recognize herself. She looked in the mirror and saw a happy looking girl with smudged makeup who looked like she'd just been having sex. Her hair looked absolutely awful! Immediately she grabbed paper towels and began fixing her hair and make-up.

When she looked somewhat more presentable, she took a long deep breath and stared at her reflection in the mirror. "Are you really about to have sex with your pseudo-boyfriend?" She asked herself. Out loud, unfortunately.

"Honey, he don't got to be your boyfriend for you to fuck him."

Blair immediately blushed at the stranger's input. "Was I talking to you?" She snapped at the woman. "No!" And with that she stomped out of the bathroom and back out into the club. She was halfway to the door when she saw Chuck at the bar chatting up some scantily clad whore.

Her stomach fell and she could only stare at the scene before her in horror. Of course, he was doing this. He was Chuck Bass. For a brief second she'd forgotten that she'd been out with Manhattan's most notorious womanizer. Of course he wanted to sleep with her. He wanted to be able to tell people that he'd taken Blair Waldorf's virginity. It was all a game to him, and suddenly she was furious with herself for allowing herself to think that she really was in a relationship with Chuck. She wasn't, and she was about to tell him this when the cops showed up and arrested both him and the woman he'd been chatting up.

All Blair could do was stare. Leave it to Chuck Bass to get arrested for solicitation while she was trying to decide if she was really going to give him her virginity. She just felt so stupid for thinking that everything was different now that she'd chosen Chuck over Nate.

Numbly she walked out to Chuck's limo and sat in the back. She stared at her cell phone for a very long while before making a decision. With a long deep breath, she dialed Nate's phone, hoping against hope that he would answer the phone.

"Blair?" He finally answered on the last ring. "What? Get ditched by Chuck already?"

She willed herself not to cry over how true Nate's words were; she refused to cry over Chuck Bass anyway. "That picture wasn't what it looks like. It was a goodbye kiss. I made a mistake, Nate."

He was quiet for awhile before finally saying, "But that night at the Palace…"

"It was the only time that it happened." She lied again. "That was it. I only kissed him, and it was a mistake." She took a deep breath before pulling out the big guns. "Daddy left Mother. For a man named Roman."

"Blair." Nate sighed and immediately Blair knew she'd won. "I'm so sorry. Do you want me to come over?"

"In a half hour?" She asked. "There's something I need to do first."

"Alright. I'll be there."

"I love you Nate Archibald." She forced out.

"I love you, too."

And with that Blair hung up the phone, feeling sick to her stomach. Immediately she opened the door to the limo and began throwing up, not caring who was looking. It felt wrong to her somehow to choose Nate over Chuck, but it was the only thing that she could do. Daddy had warned her, and she knew that she was going to get burnt by Chuck. She just hadn't realized how quickly her pseudo-relationship with Chuck would self-destruct.

When she was done throwing up, she crawled all the way back into the limo and lay on the bench, awaiting Chuck's phone call. The second she got a call from a restricted number, she snatched it up. "Chuck?"

"I'm sorry, Blair." He said upon greeting. "This girl started talking to me, and I tried to explain to her that I was waiting for someone, but she just wouldn't listen. Apparently the cops got the wrong impression."

"What precinct are you at?" She asked, suddenly feeling even worse for what she'd just done, and the feeling only got worse when she hung up on Chuck immediately after he told her where they'd taken him this time.

She threw up one more time before instructing the driver where to go.

* * *

**X.O.X.O****.**

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**

When they arrived at the precinct, she walked right up to Officer Morales. "Do you have a pen and paper?" She asked before he could even ask her if she was here to pick up Cassanova.

He shot her a strange look, but gave her what she asked for.

Blair took a deep breath before writing down: _I'm sorry, but I can't do this any more._ Then she looked back up at Officer Morales. "How much do I need to pay?"

She paid his fees and signed him out before handing Officer Morales the note. "Can you give this to him, and tell him that his limo and driver are waiting for him outside?" Blair could feel the tears on her cheeks already.

"What are you doing?" Officer Morales asked her slowly.

She gave a bitter tear-filled laugh. "Breaking up with him." And with that, she turned on her heal, stalked out of the precinct and began walking down the street, not even making an attempt to hail a cab.

At first she'd thought that it was the right thing to do, but now she just couldn't help but feel incredibly guilty. She'd written Chuck out of her life and signed herself away to be in a relationship with a guy who'd betrayed his best friend. It was horrible, but she knew she could never be in a real relationship with Chuck. She couldn't trust him.

"Blair!"

She turned and found Chuck chasing her down the street. "I can't do it, Chuck." She kept walking, refusing to let him see her cry.

"Blair!" He grabbed hold of her arm, and spun her around to face him. A startled look appeared on his face and he immediately wiped a tear away with his thumb. "Blair…" His voice was softer now.

She just shook her head at him. "I can't do it, Chuck. I can't. This isn't working. I miss Serena, and Nate…" She started crying again, but moved away when he tried to wipe the tears away. "Nate and I are back together. I can't play these games. You're my best friend without Serena here. If I'm with Nate then I still have my best friend and he still has his. It's for the best Chuck."

He just stared at her.

"I'm sorry." She whispered out before slipping away from him and moving to hail a cab.

"At least let me take you home." He finally managed to say.

Blair shook her head. "No. I need to sleep in my own bed tonight."

It was the worst night of sleep she'd had since the night she found out that Serena was gone at boarding school. She knew right then and there that she'd made the worst mistake in her life, but there was nothing she could do about it now.


End file.
